17539-80-9

Upstream product

• 96-09-3 styrene oxide 
• 622-58-2 p-Tolylisocyanate 
• 124-38-9 carbon dioxide 
• 106-49-0 p-toluidine 
• 4427-92-3 4-Phenyl-1,3-dioxolan-2-one 

Relevant academic research and scientific papers

Squaramide–Quaternary Ammonium Salt as an Effective Binary Organocatalytic System for Oxazolidinone Synthesis from Isocyanates and Epoxides

Squaramide–quaternary ammonium salt is illustrated as a simple, tunable, and competent metal-free binary catalytic platform for the atom-economic conversion of epoxides and isocyanates into oxazolidinones. Although, various metal catalysts have been employed for the title reaction, application of organocatalysis is scarce. At first, a rational survey of catalytic activity of several air-stable and architecturally distinct squaramides was undertaken. Thereafter, the impact on catalytic capability of different parameters, such as temperature, catalyst loading, and nature of nucleophiles, was examined. This binary organocatalytic system for the oxazolidinone synthesis, composed of a squaramide entity along with a suitable halide anion, was applied to the challenging conversion of a plethora of alkyl- and aryl-substituted epoxides– including disubstituted and enantioenriched ones– and isocyanates into the corresponding oxazolidinones in high-to-excellent yields. The time-dependent formation of oxazolidinone from epoxide and isocyanate was monitored by FTIR-ATR and 1H NMR spectroscopy and the scalability of this process was also described. In light of 1H NMR experiment, a hydrogen-bonding/anion-binding mechanism was proposed wherein the nucleophilic ring-opening operation, and oxo- and carbamate-anions stabilization occur cooperatively towards isocyanate fixation.

Potassium phosphate-catalyzed one-pot synthesis of 3-aryl-2-oxazolidinones from epoxides, amines, and atmospheric carbon dioxide

Potassium phosphate was found to be a highly active catalyst in the three-component cycloaddition of amines, epoxides, and carbon dioxide in DMF at ambient temperature to form 3-aryl-2-oxazolidinones. Atmospheric CO2 and a broad range of amines were employed in this transformation. Aryl isocyanate and 1,2-aminoalcohol were generated in situ as key intermediates. This one-pot reaction is applicable to a variety of terminal epoxides and amines. The key advantages are high yields, simple work-up, inexpensive catalysts, and a practical ten gram-scale synthesis.

Isocyanurate Formation During Oxazolidinone Synthesis from Epoxides and Isocyanates Catalysed by a Chromium(Salphen) Complex

Chromium(salphen) complex 10 is found to be a catalyst for the preparation of oxazolidinones from epoxides and isocyanates. Using the optimal reaction conditions (1.5 mol % of chromium(salphen) complex 10 at 80 °C in toluene for 4 hours), six epoxides wer

Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalysed by Aluminium Heteroscorpionate Complexes

The combination of an aluminium(heteroscorpionate) complex and tetrabutylammonium bromide acts as a highly efficient catalyst system for the synthesis of oxazolidinones from epoxides and isocyanates. Twenty two complexes were tested derived from a range o

VanadiumV(salen) catalysed synthesis of oxazolidinones from epoxides and isocyanates

The combination of a vanadiumV(salen) complex V +O(salen) EtOSO3- and tetrabutylammonium bromide forms a highly active catalyst system for the reaction between epoxides and isocyanates leading to oxazolidinones.

Bimetallic aluminum(salen) catalyzed synthesis of oxazolidinones from epoxides and isocyanates

The bimetallic aluminum(salen) complex [Al(salen)]2O is shown to catalyze the synthesis of oxazolidinones from epoxides and isocyanates. The reaction is demonstrated to proceed with overall retention of epoxide stereochemistry, and both aromati